


Stuck At A Crossroads

by deaneedscas



Category: Supernatural
Genre: Alternate Universe, Angst, Developing Friendships, Enemies to Friends to Lovers, F/F, F/M, Fluff, Internalized Homophobia, M/M, Multi, Music, Mutual Pining, Small Towns
Language: English
Status: In-Progress
Published: 2020-12-31
Updated: 2021-01-31
Packaged: 2021-03-11 04:27:54
Rating: General Audiences
Warnings: Graphic Depictions Of Violence
Chapters: 3
Words: 3,910
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28449174
Author URL: https://archiveofourown.org/users/deaneedscas/pseuds/deaneedscas
Summary: Dean could’ve fooled anyone with that big, gorgeous smile. He was hurting on the inside but he didn’t ever show it. At least, not until he met him. No. Not until Castiel.
Relationships: Castiel/Dean Winchester, Charlie Bradbury/Jo Harvelle, Eileen Leahy/Sam Winchester
Comments: 3
Kudos: 16





	1. Chapter 1

**Author's Note:**

> i’m so fucking sorry for any pain i cause you with this, but i still hope that you enjoy it nonetheless.

It was a beautiful, sunny Thursday afternoon, bird’s were singing their song’s, and on the sidewalk of Hatten st. walked a lonely boy by the name of Dean Winchester.

Crash

“Watch where the fuck you’re going!” He spat.

“Sorry.” He spoke in what was less than a whisper as he tried to gather his books from the ground.

Dean kept walking.

It was a mistake to stay.

The boy with the small voice turned back to look at him, as Dean was receding into the skyline.

Poor him.

He never would’ve had a chance anyways and he knew it, because being gay was a sin, that’s what his mother and father always told him growing up in the church.

“ _Castiel, you’ll go to hell_ ”

They always said it, so he was sure of it. He had to push down his every urge. But now he was longing to be touched by the boy whom bumped into him on the sidewalk, and though he was not very nice to Castiel that hadn’t seemed to matter to him.

He was feeling something, he just didn’t know what yet.

Dean felt it too. His whole walk home he felt a tingle in his arms, and a sting in his chest.

The second he entered the front door he heard the yelling, along with glass shattering, Graysin’s choked cries, and Sam’s shouting pleas for his parents to stop fighting.

Dean bolted into the dining room.

“EVERYBODY STOP!”

They all looked at Dean. Graysin still sobbing in her high-chair.

“This is none of your business Dean, you better just take them and go upstairs. It’s grownup stuff, son.” John snarled.

Dean rounded the table quickly freeing Graysin from the high-chair and holding her close to his chest, rubbing her back and cooing to calm her. She gripped his shirt tight and cried silently.

Dean stared up harshly at John. There was so much more he wanted to say to his father, but today wasn’t the day for that.

“Let’s go, Sammy.”

And just as they were walking up the stairs, the door bell rang.

“I’ll get it. Mary you clean this fucking mess up, we’ll continue our talk later.”

John walked toward the door and that was Dean’s cue to finish the ascent up the stairway and to his room with his little brother by his side and his baby sister on his hip. He swore to protect them everyday of his life, and he did.

That was just another evening in the Winchester household. So normal to them all.

Castiel on the other hand, he laid in his bed gazing up at the ceiling while one of his many Frank Ocean vinyls played softly on his baby blue record player.

His _favorite_ song.

“White Ferrari, huh?”

Castiel jumped from his bed.

“Anael, what are you doing back so soon? Thought you were gonna be gone for another two days?” Cas hugged his older sister.

“Well I just missed ya’ too much, kiddo!” She fluffed his hair.

“So, you didn’t answer my question...”

“What question?”

“White Ferrari... What’s the occasion, Cas? Find a new love?” She teased.

“What, no! That’s crazy talk”

“CAS HAS A BOYFRIEND, CAS HAS A BOYFRIE-“ Cas covered her mouth in a hurry.

“SHUSH, be quiet! The whole world doesn’t need to know you idiot!”

They sat down on Cas’ bed.

“Fine, jezz. Can’t even poke fun at my little brother anymore? This is so lame, you’re such a party pooper, Cas.”

Silence.

And then.

“So, whose the boy?” Anael turned her full attention over to her young brother, waiting for an answer.

He breathed a sigh.

“Dean”

“Winchester? From church?”

“Yeah.”

“Oh, Cas... No. That kid is bad news Castiel!”

“How so?”

“Okay, well, you didn’t hear this from me but rumor has it that he beat up that kid Jimmy Novak from down the street.”

“The really skinny, small Jimmy?”

“Yeah.”

“Wow”

“I wouldn’t hang around with him if i were you. He’s a bad influence.”

That wasn’t true though, and Cas knew it. Dean would never do all of these thing’s that everyone always said he did. No, not _his_ Dean. Cas was going to show them all. First, he had to actually finally muster up the courage to even talk to Dean, and that was all it’s own challenge.

But at this point, what _couldn’t_ Castiel Shurley handle?


	2. Chapter 2

**Notes for the Chapter:**

> i’m so sorry this chapter took longer than expected to get out, it’s just hard for me to write at times, but it’s finally done!!

June 11th 2017

_ Dear Ruby, _

_ I’m sorry this is how we have to talk now, I should’ve never let it get that far, so i’m sorry. _

_ I hope you’re safe. _

_ How’s school going? What are you learning? Do they make you do prayers every morning? How is Meg doing? Is she okay? How was the move? _

_ I just hope everything is going okay out there. Going better for all of you guys than it did when you were here, I know it was hard. _

_ Tell Meg I said Hello. _

_ Until Next Time, _

_ -Your Sammy _

There was a pause as Sam took one last look at the letter, then folded it and tucked it away into the already stamped envelope.

He missed Ruby dearly, she was his first friend since Jessica.

Sam walked down the stairs, shoulders slumped, letter in hand.

“Hey mom, could you give me a ride after church?” The young boy asked his mother.

“Of course honey, where to?”

“The post office. And then the cemetery.”

“The cemetery?” Mary was taken aback.

She wouldn’t have thought in a million years that Sammy would ever want to go back there after the funeral.

But she obliged.

“DEAN, WE GOTTA GO! HURRY PLEASE!” Mary shouted up the stairs.

“I’M COMING, I’M COMING” Dean shouted back.

He quickly emerged from his room, struggling to put on one of his dress shoes. He descended the staircase while tying his tie.

“Let’s go boy’s, your dad is already waiting in the car with Graysin” Mary said, pointing toward the door.

They all walked out. Mary’s dress was blowing in the summer breeze, her blonde hair flowing down her back curled slightly at the ends.

“What’s that?” Dean asked his little brother, noticing the sealed envelope in Sam’s fidgeting hands as he clicked his seat belt in place.

“It’s a letter.” Sam stated blankly.

“A letter? For who?”

“For ruby.”

“Ruby? Sammy-“

“Don’t patronize me okay, Dean!”

“Fine, suit yourself”

And with that they set off.

The whole ride there Sam couldn’t get his mind off Ruby. He missed her.

_ “Ruby, where the Hell do you think you’re going?” _

_ “Dad! Hey, um-“ _

_ “I asked you a question young lady. Where in the Hell do you think you’re going at midnight?” _

_ “Nowhere, I just-“ _

_ “BULLSHIT! You got your shoes on and everything! You were sneakin’ off to see that Winchester kid again I bet! Huh? Weren’t ya’?” _

_ “No dad, it’s nothing like that! I was just going to go study at Jo’s house.” _

_ “You are lyin’ through your teeth little girl!” _

_ “AHH” _

_ “WHAT DID I TELL YOU ABOUT SEEIN’ THAT BOY, HUH RUBY? WHAT DID I TELL YA’?” _

_ “STOP, PLEASE!” _

Sam remembered hearing it all. He remembered having to bust through the front door. He remembered finding Ruby on the floor seven shades of black and blue with blood trickling from opened wounds. He remembered threatening Mr. Masters. He remembered Mr. Masters threatening him. He remembered calling the police. He remembered seeing Mr. Masters shoved into the back of a squad car. He remembered seeing Mrs. Masters and Meg crying holding Ruby. He remembered seeing them wheel Ruby into an Ambulance. And he remembered, clear as day, seeing that same Ambulance drive away with his half-dead lover strapped to a gurnee in the back.

Sam always blamed himself. No one else did. It wasn’t Sam’s fault Mr. Masters had a temper. But he still blamed himself for everything. For Ruby almost dying that night. He could’ve lost her. Just like he lost Jess.

“-I think it is, but I don’t know.”

“Hey Sammy, what’s Ruby’s favorite kind of pie?”

“Blueberry. Same as mine.”

“That’s just what I thought”

“Why do you guys wanna know Ruby’s favorite pie flavor?”

“We were just talking and thinking about sending her a pie.”

“Oh.”

“That okay?”

“Yeah, I don’t care.”

Just as the final cord struck in Black Dog, that had been playing on the cars radio, they pulled into their space in the church parking lot.

Castiel was standing outside with his parents talking to Pastor Jim.

The Winchester family exited their car.

And Cas saw him.  _Dean_.

“Okay well, I must be getting inside to rehearse with the choir real quick before we start. It was very nice seeing and talking to you again Pastor.” Castiel shook his hand quickly and sped inside to take his place standing by Anael.

“What was that all about?” Anael asked a slightly out of breath Castiel.

“Huh?”

“You came running back in here like a bat out of hell, what was that?”

“Winchester” Castiel whispered, as if being a Winchester was a secret. They were known in town notoriously for causing chaos and destruction.

Namely John.

He owned the town’s body shop. He’d fix someone’s head gaskets if they blew, or their motor if it ran out, or a tire if it popped. Whenever someone was having car troubles they’d say “go to John Winchester, he’s your guy” but that was just about all he was good for to the townsfolk. Just another helping hand, and nothing more. If only people knew why John was the way he was now. If only  _ they saw  _ what  _John saw_.

The people talking outside the front of the Church started to filter through it’s doors, going into the main hall for mass.

As they entered the choir was singing Let It Shine.

It was then Dean noticed  _ him _ . He  _ really _ noticed him. He  _ saw _ Castiel. And for a second Dean could’ve sworn Cas was an Angel, with wings. Wings he just wanted to reach out and touch softly. Wings he wanted to protect him.

“ _Wow_ ”  Dean said subconsciously.

“Wow what?” Mary asked.

“Uh, The choir. They just sing so beautifully. I guess I never really noticed before how good they are.” He was only half lying.

“They do sing beautifully, don’t they?”Mary remarked, walking away to take her seat.

Dean followed behind his mother slowly, not wanting to take his eyes off Castiel, as if he would just fly away if he did.

_ stop dean, you can’t think like that _

_ being gay is a sin _

_ it’s a sin _

_ a sin _

_ you’re sin _

_ you’re a sinner _

_ you’re going to go to hell _

_ you’ll never see the gates _

_ hell _

_ hell _

_ hell _

Dean tried to shake his head to make the intrusive thoughts go away.

The choir continued to sing until the song was over and then mass started.

The whole time Dean could take his mind off Castiel. Dean knew who he was. He’d known Castiel since they were kid’s, but they were never really friends. They were loners and didn’t run with any crowds in the town. They were both kind of mysterious to one another and that’s what pulled them in.

_ The thrill of the chase. _

Dean wanted to know if Castiel had a record player and records like his very own at home. Was he into cars too? So many questions Dean wondered, yet no answers.

Dean knew now he had to talk to this boy. He had to know him. But how would a harsh blunt kid like Dean Winchester get a soft shy kid like Castiel Shurley to even speak to him?

_ Then it was like a bulb went off in his head, and he knew. _

_ He knew. _

_ “Library.” _

Before they all knew it mass had ended and the choir sung Hallelujah to close.

Dean was  _ mesmerized _ by Castiel.

He was falling head over heals.

“Come on boy’s, lets go.” Mary said, taking Graysin from John’s arms.

“Where’s dad going?” Sam asked.

Dean took Graysin from Mary.

“Hi” He cooed to her. She smiled.

“Out with some old war buddies.”

“Welp, guess he’s gonna be gone the whole day then” Dean half asked

“I assume so.”

“Hey, mom. I think i’m gonna go to the library.” Dean stated as Graysin played with his fingers.

“The library?” Mary wasn’t convinced.

Mary took Graysin back from him.

“Yeah”

“Okay then. Do you wanna change first?”

Dean looked down at his church suit.

“No, i’m fine. I’m just gonna walk there too.”

“Oh, okay.” Mary knew.

Dean was being quite literal, and started walking away to the direction of the library.

“Well, okay then.”

“He’s in love again, isn’t he?” Sam asked.

“I think so, Sammy.”

“Great”

“Let’s just hope this doesn’t end in a disaster like what happened with Cassie.” Mary divulged.

“True that”

When they got to the car Mary strapped Graysin into her carseat in the back, while Sam got into the front passenger seat.

“Post office?” Mary asked, looking down over to Sam, her seat belt buckled with both hands on the steering wheel ready to drive out.

“Post office.” Sam stated with a nod of his head.

Once they got there Sam quickly placed his letter to Ruby into a drop box and ran off back to the car.

Then they drove to the cemetery, and the ride was silent. You could hear a pin drop.

“Do you want me to come with you?” Mary asked as they pulled up the drive.

“No. I have to do this.”

“Okay, Sammy”

Sam exited the car and made his way to Jessica’s grave.

The second he saw the picture of her and her name engraved on her headstone he fell to the ground on his knees, sobbing, with his head hung somberly.

“Jess.  Jessica, i’m so sorry. I never meant for any of this to happen. Please, just come back,” Sam punched the ground. “Come back to me, damnit!”

Jessica was Sam’s first friend.

_ His First Love. _

Sam couldn’t stand to live without her. She was always by his side, since day one. And then she got ripped away from him so cruelly. Sam always blamed himself,  for everything.  He blamed himself for Jess, and for Ruby. But Ruby wasn’t his fault. No. Not really. And Jess. What happened to her was the farthest thing from it. Yet, Sam still took the blame all on his own. He held that burden like an anvil on his shoulders.

“I love you, Jessica”

**Notes for the Chapter:**

> how’d you guys like it? did it make you cry? it definitely made me cry a few times writing it, especially the ruby flashback.


	3. Chapter 3

**Notes for the Chapter:**

> hey guys! sorry it’s taken me so long to get this chapter out. as a lot of you know there were time where i was blocked or had no ideas or had no motivation. but chapter three is finally here now, so read up !!

Castiel stared out the window, thinking fondly of the memory of Dean from the day before.

“He was just so kind to me. He hadn’t been much before. He’s never even really talked to me. I don’t think we’ve had an actual conversation since we were kids. And it was so natural too, and I didn’t feel nervous like I thought I would. It was freeing in a way, if that makes any sense.”

“It does! I totally understand what you’re saying, I felt the same way with Eileen.” Anael assured Cas.

“He’s so pretty Anael! He’s the prettiest boy in Garrison.” Cas said happily.

And as if it was almost planned by god, Bad Religion started playing through the car’s speakers.

“Taxi driver, be my shrink for the hour.” Cas and Anael sung along.

Meanwhile, on the other side of town...

Dean stood near the edge of the cliff, looking out at the town as the sun began to finally set, bringing an end to the day.

He was in deep thought. About  Castiel .

“I just- I don’t know Jo. I saw him, so much differently than I have before. I mean he looked like an angel standing up there and singing. His voice. Oh man, his voice. It was so beautiful, Jo. You should’ve heard him. It was so beautiful.” Dean explained, gazing off at the scenery in front of him.

“You wanna know something?” Jo said with a smirk on her face.

“What?” Dean was curious.

“I felt almost the exact same way about Charlie when I got to know her.”

“-But boy you need prayer, I guess it couldn’t hurt me.”

“Hey, Jo”

“Yeah Dean?”

“What’s that song playing on the radio?”

“Bad Religion by Frank Ocean.”

“This unrequited love. To me, it's nothin' but a one-man cult. And cyanide in my styrofoam cup. I can never make him love me. Never make him love me. Love me, love me. Love me-“

“I like it” Dean stated, with a small smile.

“-Love me. Love me, love me. Love me, love me. Love me, love. Taxi driver, I swear i've got three lives, balanced on my head like steak knives. I can't tell you the truth about my disguise. I can't trust no one.-“

“Anael, I wanna talk to him again. But I don’t know how I would even do that”

“Figure out a place he likes to go and pretend to run into him there, that’s what I used to do.”

“If it brings me to my knees, it's a bad religion. Oh, unrequited love. To me, it's nothin' but a one-man cult. And cyanide in my styrofoam cup. I can never make him love me. Never make him love me. No, no, ahh.

It's a, it's a bad religion. To be in love with someone. Who could never love you. Oh-oh-oh, only bad, only bad religion. Could have me feeling the way I do”

Cas sang along ‘til the song ended.

“That’s how I feel about it sometimes.”

“What?” Anael asked.

“That me liking him is a bad religion. That I shouldn’t like him because being gay is a sin, and i’m a sinner for indulging. And that my love is unrequited, because it probably fucking is!”

“Stop saying stuff like that, Castiel! Being gay is  _ not _ a sin and you are  _ not _ a sinner! You are  not going to hell for being gay! Stop letting what mom and dad said get to you, Cas. You’re stronger than that!”

“It’s true, Anael!”

“IT’S NOT!”

“I want to be honest, I want to be bad. I want to destroy you, I want to move-“

“Whatever. Just drop me off at the park.” Cas said, irritated by the conversation.

“I thought we were going home, Cas”

“You can, I just wanna go to the park and clear my head.”

“Fine.”

The second Anael pulled up to the park Cas took his phone and got out of the car.

Just down the sidewalk Dean and Jo were walking, and talking about nothing. Then Dean spotted someone on the swings. Jo followed his gaze.

_ Castiel. The beautiful boy with the angel wings. _

“You wanna go talk to him?” Jo whispered.

“Nah, it’s fine. I’m supposed to spend the night with my best friend.” Dean slung his arm over Jo’s shoulder with a smirk.

She pushed him toward the park.

“Go talk to the boy, Winchester.”

Dean looked back at Cas, then at Jo, then to Cas again, then back to Jo once more.

Jo mouthed a “go” shooing Dean with her hands. And Dean walked over. In short strides he walked, nervous to talk to this  _ angelic _ boy.

“Hey”

Cas jumped a little and looked up at Dean.

“I’m sorry, did I scare you?”

“Just a little” Cas breathed a small laugh.

“Sorry”

“It’s fine.”

A pause.

“Mind if I sit?”

“No, not at all. Go right ahead.” Cas gestured toward the empty swing next to him.

“So, what are you doing here by yourself at this time of night?” Dean asked, swinging himself ever so slightly.

“I just... Needed to clear my head, you know?”

“Yeah, I know the feeling.”

“What about you, what are you doing out here?” Cas was looking so intently at Dean.

“Well, I was hanging out with Jo, but then we saw you and she made me come over here to talk to you.”

“So, you didn’t want to, or-“

“No no no, it’s nothing like that! I was just nervous is all.”

“Nervous, huh? Are you nervous right now?”

Dean gulped.

“Maybe a little.”

“Don’t be. I’ve got you.”

And just like, Cas was kissing Dean.

Dean was shocked at first but quickly kissed back.

He felt something wrap around him. Big, soft, comforting.

_ Wings. _

“DEAN”

Dean heard Jo’s voice call out but he didn’t care.

“DEAN” Jo screamed in Dean’s ear

“AH”

Dean shot up, heaving.

“Did you have a nightmare or something?”

“No. The complete opposite actually.”

Just down the way, at the Shurley residence, Anael was making breakfast for Cas and Gabe when the home phone rang.

“Don’t pick it up!” Gabe said.

“Oh, come on! That movie you watched last night isn’t real!” Cas shouted.

“Guys! It could be dad. I have to answer it.”

Anael picked up the phone.

“Is she serious, man?” Gabe whispered.

“I don’t know” Cas shrugged.

“Dean.”

“Dean?” Cas whispered.

“Winchester?” Gabe asked.

“I’d assume so.” Cas whispered back.

“You wanna talk to Cas?”

Cas jumped up from the barstool

“Anael give me the phone.”

“I don’t know Dean, he’s kinda busy right now.” Anael smirked down at Cas.

“Give me the phone!” Cas kept reaching for it.

“Busy?” Dean asked.

Jo was staring at him confused.

“Yeah, Castiel is  _ super _ busy with-“

“I’M NOT! I’M NOT BUSY!” Cas yelled, still reaching for the phone and push Anael with his hip.

“Was that Cas?”

“No, that’s our Parakeet!”

“I’M NOT A FUCKING BIRD, ANAEL!”

“Sounds an awful lot like Cas” Dean laughed.

“It’s not!”

“YES IT IS, IT’S ME DEAN!”

“Cas...”

“What the hell is happening?” Jo asked.

“I don’t know” Dean sighed and shrugged.

“DEAN, DEAN IT’S-“

And then the line went dead.

“ANAEL, WHAT THE HELL?”

“I’m not letting you get involved with him.”

“WHY NOT?”

“First off lower your fucking tone with me. I’m your big sister, I know what’s best for you.”

“Not this, Anael. Okay? Not with this. And I thought you were happy that i’d talk to him the other day, I thought you wanted this for me after our talk yesterday”

“I never said any of that. I was just happy because you were. I didn’t want to make you upset, that’s why I gave you that advice, but Cas...  _Not Dean_. ”

“Whatever.”

Cas walked off to his room, and Gabe went after him.

“What the hell just happened?” Jo asked.

“I have no clue.”

“Let’s just go out.”

“Where? There’s nothing to do in this town, JoJo.”

“We’ll figure something out. You just need to get your mind off Cas for the day.”

Dean rolled his eyes.

“Hey!” Jo smacked the back of his head.

“Ouch!” Dean rubbed his head.

“It’s true!” Jo pointed.

“Yeah, yeah, yeah. Let’s go.”

All My Love by Led Zeppelin played softly, as Gabe entered the room.

Cas turned his head to see who it was.

“What, you come here to scold me too?”

“No. The opposite actually.” Gabe assured, sitting in Cas’ bed.

“Huh?”

“Yep. I really really think you should go for ‘em Cas.”

“You’re serious?” Cas sat up.

“Hell’s yeah!”

“Okay but like, what do I even do? Like how would I-“

“Hey, hey, hey! Slow your role. We’ll take it one step at a time.”

Cas nodded.

“While I’m here I’m gonna be your  _wing man_!” Gabe said with a smile, patting Cas’ shoulder.

They were both excited.

Cas was going to finally get  _ the boy of his dreams. _

_ What a wonderful world._

**Notes for the Chapter:**

> so... ehehe,, pls don’t hate me for that one. thx

**Author's Note:**

> so, what’d you think besties?


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